Methyl iodide → 1-Chloro-2-methoxy-4-methylbenzene

Participants

Reaction Conditions

Reaction Steps

2-Chloro-5-methylphenol (50 mmol, 7.13 g), NaOH pellets (60 mmol, 2.4 g), and methanol (50 ml) were stirred together until a homogeneous solution was obtained. The flask was cooled to 0° C., and methyl iodide (60 mmol, 3.77 ml) was added. The reaction was warmed over 2 hours to ambient and stirred for 16 hours. Reaction was still incomplete by thin layer chromatography; additional NaOH (˜300 mg) and CH3I (˜5 ml) was introduced, and stirring continued for another 24 hours. TLC again indicated incomplete conversion, so additional time and reagents were again applied. The mixture was at length concentrated, diluted with water (50 ml), and extracted with methylene chloride (2×25 ml). The combined organic layer was dried (MgSO4), filtered through silica, and concentrated to afford the title compound as an oil (5.09 g, 65%).

Provenance & Evidence